Cucumber Quest: Basically if Paper Mario the Thousand Year Door was a comic

[Kantaki]

Personally, I suspect the Dream Oracle that hands this quest to hero after hero to have some nasty (for this comic) objective as to why she helps keep this cycle going.

Right. The Oracle. I had kinda forgotten about her*.

Yes, she's most likely the big bad.

*That proves it. Only a devastatingly clever villain would manage that.